Non-aqueous dispersions of relatively high molecular weight epoxy resins

Abstract

Non-aqueous dispersions are disclosed which contain (A) a relatively high molecular weight epoxy resin, (B) a non-aqueous dispersion medium, and (C) a dispersant such as a copolymer of (1) at least one polymerizable ethylenically unsaturated monomer containing a group reactive with an epoxy group and (2) at least one polymerizable ethylenically unsaturated monomer free of any groups reactive with an epoxy group. These dispersions are useful in coatings, electrical or structural laminates or composites, body solders, adhesives, caulking compounds, casting compounds, filament winding and the like.

We claim: 
     
       1. A non-aqueous dispersion comprising (A) at least one epoxy resin having an average epoxide equivalent weight of at least about 475 and a Durran's softening point of at least about 70° C.;   (B) a non-aqueous dispersion medium; and   (C) a dispersant composition comprising a polymer prepared from (1) at least one polymerizable ethylenically unsaturated monomer containing a group reactive with an epoxy group and   (2) at least one polymerizable ethylenically unsaturated monomer free of groups reactive with an epoxy group; wherein (i) component (A) is present in an amount of from about 30 to about 75, percent by weight of the combined weight of components (A), (B) and (C);   (ii) component (B) is present in an amount of from about 20 to about 60, percent by weight of the combined weight of components (A), (B), and (C);   (iii) component (C) is present in an amount of from about 1 to about 60, percent by weight of the combined weight of components (A), (B) and (C);   (iv) component (C-1) is present in an amount which provides from about 0.1 to about 100, percent by weight of the combined weight of components (C-1) and (C-2); and   (v) component (C-2) is present in an amount which provides from about 0 to about 99.9, percent by weight of the combined weight of components (C-1) and (C-2).       
     
     
       2. A non-aqueous dispersion of claim 1 (i) component (A) is present in an amount of from about 50 to about 75, percent by weight of the combined weight of components (A), (B) and (C);   (ii) component (B) is present in an amount of from about 20 to about 45, percent by weight of the combined weight of components (A), (B) and (C);   (iii) component (C) is present in an amount of from about 5 to about 21, percent by weight of the combined weight of components (A), (B) and (C); and   (iv) component (C-1) is present in an amount which provides from about 0.5 to about 6, percent by weight of the combined weight of components (C-1) and (C-2).   
     
     
       3. A non-aqueous dispersion of claim 2 wherein (i) component (A) is at least one epoxy resin represented by formulas (I), (II) or (III) in the specification wherein each A is independently a divalent hydrocarbon group having from one to about 8 carbon atoms, --O--, --S--, --S--S--, ##STR4##  each A' is independently a divalent hydrocarbon group having from 1 to about 8 carbon atoms; each R is independently hydrogen or an alkyl group having from 1 to about 4 carbon atoms; R' is hydrogen or a hydrocarbyl group having from 1 to about 8 carbon atoms; each X is independently hydrogen, chlorine, bromine or a hydrocarbyl or hydrocarbyloxy group having from 1 to about 8 carbon atoms; n has an average value of zero or 1; n' has an average value of from 2 to about 15 and n" has an average value of from about 2.01 to about 8;   (ii) component (B) is an aromatic or aliphatic hydrocarbon material having from about 6 to about 28 carbon atoms or mixture thereof;   (iii) component (C-1) is at least one monomer represented by formula (IV) in the specification wherein R is hydrogen; each R 1  is independently hydrogen or a hydrocarbyl group having from 1 to about 20 carbon atoms; R 2  is hydrogen, halogen or a hydrocarbyl group having from 1 to about 20 carbon atoms which hydrocarbyl group may or may not be substituted with a --C.tbd.N group and R 3  is hydrogen, halogen, or a hydrocarbyl group having from 1 to about 20 carbon atoms;   (iv) component (C-2) is at least one monomer represented by formulas (IV) or (V) in the specification wherein R is a hydrocarbyl group having from 1 to about 20 carbon atoms; each R 1  is independently hydrogen or a hydrocarbyl group having from 1 to about 20 carbon atoms; R 2  is hydrogen, halogen or a hydrocarbyl group having from 1 to about 20 carbon atoms which hydrocarbyl groups may or may not be substituted with a --C.tbd.N group and R 3  is hydrogen, halogen or a hydrocarbyl group having from 1 to about 20 carbon atoms.   
     
     
       4. A non-aqueous dispersion of claim 3 wherein (i) component (A) is at least one epoxy resin represented by formula (I) wherein A is a divalent hydrocarbyl group, each X is hydrogen, n has a value of 1 and n' has a value from 2 to about 15;   (ii) component (B) is xylene, hexane, an isoparaffinic hydrocarbon fraction having a boiling range of from about 116° C. to about 134° C., an isoparafinnic hydrocarbon fraction having a boiling range of from about 207° C. to about 260° C., an aromatic hydrocarbon fraction having a boiling range of from about 156° C. to about 180° C. or any combination thereof;   (iii) component (C-1) is scrylic acid, methacrylic acid or a mixture thereof; and   (iv) component (C-2) is styrene, lauryl methacrylate or a mixture thereof.   
     
     
       5. A process for preparing a non-aqueous dispersion which comprises (I) reacting (A) at least one epoxy resin having an average epoxide equivalent weight of at least about 475 and a Durran's softening point of at least about 70° C. with   (B) at least one polymerizable ethylenically unsaturated monomer containing a group reactive with an epoxy group;     (II) copolymerizing the product resulting from step (I) with (C) at least one polymerizable ethylenically unsaturated monomer free of groups reactive with an epoxy group; and     (III) dispersing the product from step (II) in (D) a non-aqueous dispersion medium; (i) component (A) is at least one epoxy resin represented by formulas (I), (II) or (III) in the specification wherein each A is independently a divalent hydrocarbon group having from one to about 8 carbon atoms, --O--, --S--, --S--S--, ##STR5##  each A' is independently a divalent hydrocarbon group having from 1 to about 8 carbon atoms; each R is independently hydrogen or an alkyl group phaving from 1 to about 4 carbon atoms; R' is hydrogen or a hydrocarbyl group having from 1 to about 8 carbon atoms; each X is independently hydrogen, chlorine, bromine or a hydrocarbyl or hydrocarbyloxy group having from 1 to about 8 carbon atoms; n has an average value of zero or 1; n' has an average value of from 2 to about 15 and n"has an average value of from about 2.01 to about 8; and is present in an amount of from about 30 to about 75 percent by weight of the combined weight of components (A), (B), (C) and (D);   (ii) component (B) is at least one monomer represented by formula (IV) in the specification wherein R is hydrogen; each R 1  is independently hydrogen or a hydrocarbyl group having from 1 to about 20 carbon atoms; R 2  is hydrogen, halogen or a hydrocarbyl group having from 1 to about 20 carbon atoms which hydrocarbyl group may or may not be substituted with a --C.tbd.N group and R 3  is hydrogen, halogen or a hydrocarbyl group having from 1 to about 20 carbon atoms and is present in an amount which provides from about 0.1 to about 100 percent by weight of the combined weight of components (B) and (C);   (iii) component (C) is at least one monomer represented by formulas (IV) or (V) in the specification wherein R is a hydrocarbyl group having from 1 to about 20 carbon atoms; each R 1  is independently hydrogen or a hydrocarbyl group having from 1 to about 20 carbon atoms; R 2  is hydrogen, halogen or a hydrocarbyl group having from 1 to about 20 carbon atoms which hydrocarbyl groups may or may not be substituted with a --C.tbd.N group and R 3  is hydrogen, halogen or a hydrocarbyl group having from 1 to about 20 carbon atoms and is present in an amount which provides; from about 0 to about 99.9 percent by weight of the combined weight of components (B) and (C); and   (iv) component (D) is present in an amount of from about 20 to about 60 percent by weight of the combined weight of components (A), (B), (C) and (D).       
     
     
       6. A process of claim 5 wherein (i) component (A) is present in an amount of from about 50 to about 75 percent by weight of the combined weight of components (A), (B), (C) and (D);   (ii) component (B) is present in an amount which provides from about 0.5 to about 6 percent by weight of the combined weight of components (B) and (C);   (iii) component (C) is present in an amount which provides; from about 94 to about 99.5 percent by weight of the combined weight of components (B) and (C); and   (iv) component (D) is present in an amount of from about 20 to about 25 percent by weight of the combined weight of components (A), (B), (C) and (D).   
     
     
       7. A process of claim 6 wherein (i) component (A) is at least one epoxy resin represented by formula (I) wherein A is a divalent hydrocarbyl group, each X is hydrogen, n has a value of 1 and n' has a value from 2 to about 15;   (ii) component (B) is acrylic acid, methacrylic acid or a mixture thereof; and   (iii) component (C) is styrene, lauryl, methacrylate or a mixture thereof; and   (iv) component (D) is xylene, hexane, an isoparaffinic solvent having a boiling range of from about 116° C. to about 134° C., an isoparaffinic hydrocarbon fraction having a boiling range of from about 207° C. to about 260° C., an aromatic hydrocarbon fraction having a boiling range of from about 156° C. to about 180° C. or any combination thereof.   
     
     
       8. The product resulting from curing a composition of claims 1, 2, 3 or 4 with a curing quantity of a suitable curing agent or a catalytic quantity of a suitable catalyst or a combination thereof. 
     
     
       9. A product comprising a substrate coated with a composition of claim 8.